Issue 14, 2010

Unprecedented parallel packing of unsymmetrical bolaamphiphiles driven by π–π stacking of cinnamoylgroups

Abstract

The self-assembly and molecular packing mode of a novel, unsymmetrical bolaamphiphile, sodium 4-(6-hydroxyhexyloxy) cinnamate (SHHC) was studied. Tube-like structures were obtained in SHHC aqueous solution at pH 9.2. Upon UV irradiation, the SHHC molecules in the system were found to undergo four-center-type photocyclodimerization and photoisomerization. The combination of IR, XRD and Zeta potential results suggested the formation of a tail-to-tail type bilayer membrane structure: the SHHC molecules stretched upright with the cinnamate headgroups toward the outside in each layer, whereas the tail OH groups of two layers remained inside and formed interlayer hydrogen bonds. This parallel packing mode of SHHC molecules in the membrane was also confirmed by the pH-induced self-assembly transition. With increasing pH from 9.2 to 12.0, the low-curvatured tubes transformed into spherical vesicles, which was in line with the increased outer leaflet head group area as increasing pH. Our results demonstrated that upon careful molecular design, the orientation of unsymmetrical bolaamphiphiles can be controlled; π–π interactions between cinnamoyl groups were found to be strong enough to drive the formation of well-oriented molecular assemblies.

Graphical abstract: Unprecedented parallel packing of unsymmetrical bolaamphiphiles driven by π–π stacking of cinnamoyl groups

Supplementary files

Article information

Article type
Paper
Submitted
05 Feb 2010
Accepted
30 Mar 2010
First published
25 May 2010

Soft Matter, 2010,6, 3282-3288

Unprecedented parallel packing of unsymmetrical bolaamphiphiles driven by π–π stacking of cinnamoyl groups

Y. Zhao, J. Zhao, Y. Yan, Z. Li and J. Huang, Soft Matter, 2010, 6, 3282 DOI: 10.1039/C002541K

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